Nickel-Catalyzed β-Boration of α,β-Unsaturated Esters and Amides with Bis(pinacolato)diboron

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Abstract

A nickel catalyst system for β-boration of α,β-unsaturated esters and amides with bis(pinacolato)diboron has been developed. The catalyst system enables the boration of di-, tri-, and tetrasubstituted substrates in good yields.

Citing Articles

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This article has been cited by 19 ACS Journal articles (5 most recent appear below).

• 

  NiCl₂(PMe₃)₂-Catalyzed Borylation of Aryl Chlorides

  Tetsuya Yamamoto, Tomoyuki Morita, Jun Takagi, and Tetsu Yamakawa
  Organic Letters2011 13 (21), 5766-5769

  • NiCl₂(PMe₃)₂-Catalyzed Borylation of Aryl Chlorides

    Tetsuya Yamamoto, Tomoyuki Morita, Jun Takagi, and Tetsu Yamakawa
    Organic Letters2011 13 (21), 5766-5769

    The cross-coupling of aryl chlorides and bis(pinacolato)diboron was achieved using NiCl2(PMe3)2 catalyst in the presence of metal 2,2,2-trifluoroethoxide. The catalyst smoothly provided the desired products regardless of a variety of functional groups and ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Copper-Catalyzed β-Boration of α,β-Unsaturated Carbonyl Compounds with Tetrahydroxydiborane

  Gary A. Molander and Silas A. McKee
  Organic Letters2011 Article ASAP

  • Copper-Catalyzed β-Boration of α,β-Unsaturated Carbonyl Compounds with Tetrahydroxydiborane

    Gary A. Molander and Silas A. McKee
    Organic Letters2011 Article ASAP

    The copper-catalyzed β-boration of α,β-unsaturated carbonyl compounds with tetrahydroxydiborane has been developed. This diboron reagent allows direct, efficient access to boronic acids and their derivatives. Primary, secondary, and tertiary α,β-...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Mechanisms of Reactions of a Lithium Boryl with Organohalides

  Man Sing Cheung, Todd B. Marder, and Zhenyang Lin
  Organometallics2011 Article ASAP

  • Mechanisms of Reactions of a Lithium Boryl with Organohalides

    Man Sing Cheung, Todd B. Marder, and Zhenyang Lin
    Organometallics2011 Article ASAP

    Reactions of the lithium boryl LiB(R′NCH═CHNR′) (R′ = 2,6-iPr2C6H3), 1, with organohalides (RX) giving RB(R′NCH═CHNR′) and/or XB(R′NCH═CHNR′) were studied computationally using density functional theory calculations at the B3LYP level. Our calculations ...

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• 

  Structure and Reactivity of a Preactivated sp²–sp³ Diboron Reagent: Catalytic Regioselective Boration of α,β-Unsaturated Conjugated Compounds

  Ming Gao, Steven B. Thorpe, Christian Kleeberg, Carla Slebodnick, Todd B. Marder, and Webster L. Santos
  The Journal of Organic Chemistry2011 Article ASAP

  • Structure and Reactivity of a Preactivated sp²–sp³ Diboron Reagent: Catalytic Regioselective Boration of α,β-Unsaturated Conjugated Compounds

    Ming Gao, Steven B. Thorpe, Christian Kleeberg, Carla Slebodnick, Todd B. Marder, and Webster L. Santos
    The Journal of Organic Chemistry2011 Article ASAP

    A novel sp2–sp3 diboron reagent has been developed for the copper-catalyzed β-boration of α,β-unsaturated conjugated compounds. The reaction proceeds under mild conditions with various substrates, i.e., α,β-unsaturated esters, ketones, nitriles, ynones, ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Impregnated Copper on Magnetite as Recyclable Catalyst for the Addition of Alkoxy Diboron Reagents to C−C Double Bonds

  Rafael Cano, Diego J. Ramón and Miguel Yus
  The Journal of Organic Chemistry2010 75 (10), 3458-3460

  • Impregnated Copper on Magnetite as Recyclable Catalyst for the Addition of Alkoxy Diboron Reagents to C−C Double Bonds

    Rafael Cano, Diego J. Ramón and Miguel Yus
    The Journal of Organic Chemistry2010 75 (10), 3458-3460

    A simple protocol for the borylation with use of impregnated copper on magnetite is described. The reactions showed a very broad scope and all type of olefins could be used with similar results. The catalyst could be easily removed by a magnet and it ...

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